Evidence of an equilibrium between selenides and osmium(viii) reagents and selenoxides and osmium(vi) reagents

Abstract

Driving the equilibrium between selenides and osmium(VIII) reagents with selenoxides and osmium(VI) by a subsequent reaction (rearrangement of allyl selenoxides to allyl alcohols or addition of osmium(VIII) species on C=C double bonds) to one side, allows the transformation of methyl geranyl selenides to linalool and of methyl citronellyl selenoxide to 6,7-dihydroxy citronellyl selenide.

Recent Developments in Metal‐Catalyzed Dihydroxylation of Alkenes

“…It was shown that both yield and enantioselectivity are influenced by the pH of the reaction medium. The procedure was also applied to practical syntheses of natural product derivatives [27]. This version of the AD reaction not only uses a more ecological co-oxidant, but also requires much less material: 87 mg of material (catalyst, ligand, base, reoxidant) is required to oxidize 1 mmol of the same alkene instead of 1400 mg when AD mix is used.…”